Protective role of a coumarin-derived schiff base scaffold against tertiary butyl hydroperoxide (TBHP)-induced oxidative impairment and cell death via MAPKs, NF-κB and mitochondria-dependent pathways

Free Radical Research

Volumn 45, Issue 5, 2011, Pages 620-637

  Ghosh, Manoranjan ^a   Manna, Prasenjit ^a   Sil, Parames C ^a  

^a BOSE INSTITUTE   (India)

Author keywords

antioxidant; cell death; CSB; cytoprotection; Hepatocyte; MAPKs; oxidative stress; TBHP

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; CASPASE 3; COUMARIN DERIVATIVE; CYTOCHROME C; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; SCHIFF BASE; TERT BUTYL HYDROPEROXIDE;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; APOPTOSIS; ARTICLE; CELL DAMAGE; CELL DEATH; CELL VIABILITY; CYTOTOXICITY; DNA FRAGMENTATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVATION; FLUORESCENCE ACTIVATED CELL SORTING; LIVER CELL; MITOCHONDRIAL MEMBRANE POTENTIAL; MOUSE; NONHUMAN; OXIDATIVE STRESS;

ANIMALS; ANTIOXIDANTS; APOPTOSIS; CASPASE 3; CELL DEATH; CELL SURVIVAL; COUMARINS; CYTOPROTECTION; DNA FRAGMENTATION; EXTRACELLULAR SIGNAL-REGULATED MAP KINASES; FREE RADICAL SCAVENGERS; FREE RADICALS; HEPATOCYTES; LIPID PEROXIDATION; MEMBRANE POTENTIAL, MITOCHONDRIAL; MICE; NF-KAPPA B; OXIDATION-REDUCTION; OXIDATIVE STRESS; REACTIVE OXYGEN SPECIES; SCHIFF BASES; TERT-BUTYLHYDROPEROXIDE;

MURINAE;

EID: 79952655577     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.3109/10715762.2011.564166     Document Type: Article

References (50)

1. nd ed. Paris: Lavoisier Publishing; 1999. p. 225-459.
2. Murray RDH. Coumarins. Nat Prod Rep 1989;8:591-624.
3. Farombi EO, Nwaokeafor IA. Anti-oxidant mechanisms of kolaviron: studies on serum lipoprotein oxidation, metal chelation and oxidative membrane damage in rats. Clin Exp Pharmacol Physiol 2005;32:667.
4. Laurin P, Ferroud D, Klich M, Dupis-Hamlin C, Mauvais P, Lassaigne P, Bonnefoy A, Musicki B. Synthesis and in vitro evaluation of novel highly potent coumarin inhibitors of gyrase. Bioorg Med Chem Lett 1999;9:2079-2084.
5. Emmanuel-Giota AA, Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, Nicolaides DN. Synthesis and biological evaluation of several 3-(coumarin-4-yl)tetrahydroisoxazole and 3-(coumarin-4-yl)dihydropyrazole derivatives. J Heterocyclic Chem 2001;38:717-722. (Pubitemid 32624712)
6. Azza AA, Abu-Hussen. Synthesis and spectroscopic studies on ternary bis-Schiff-base complexes having oxygen and/or nitrogen donors. J Coord Chem 2006;59:157-176.
7. Singh K, Barwa MS, Tyagi P. Synthesis, characterization and biological studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with bidentate Schiff bases derived by heterocyclic ketone. Eur J Med Chem 2006;41:147-153.
8. Mladenova R, Ignatova M, Manolova N, Petrova T, Rashkov I. Preparation, characterization and biological activity of Schiff base compounds derived from 8-hydroxyquinoline-2-carboxaldehyde and Jeffamines ED. Eur Polym J 2002;38:989-999. (Pubitemid 34200973)
9. Melagraki G, Afantitis A, Igglessi-Markopoulou O, Detsi A, Koufaki M, Kontogiorgis C, Hadjipavlou-Litina DJ. Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts. Eur J Med Chem 2009;44:3020-3026.
10. Kontogiorgis CA, Hadjipavlou-Litina DJ. Synthesis and biological evaluation of novel coumarin derivatives with a 7-azomethine linkage. Bioorg Med Chem Lett 2004;14:611-614. (Pubitemid 38114837)
11. Kontogiorgis CA, Hadjipavlou-Litina DJ. Synthesis and anti-inflammatory activity of coumarin derivatives. J Med Chem 2005;48:6400-6408. (Pubitemid 41428992)
12. Cawthon D, McNew R, Beers KW, Bottje WG. Evidence of mitochondrial dysfunction in broilers with pulmonary hypertension syndrome (Ascites): effect of t-butyl hydroperoxide on hepatic mitochondrial function, glutathione, and related thiols. Poult Sci 1999;78:114-124. (Pubitemid 129554730)
13. Kaur P, Kaur G, Bansal MP. Upregulation of AP1 by tertiary butylhydroperoxide induced oxidative stress and subsequent effect on spermatogenesis in mice testis. Mol Cell Biochem 2008;308:177-181. (Pubitemid 351167859)
14. Tarín JJ, Pérez-Albalá S, García-Pérez MA, Cano A. Effect of dietary supplementation with a mixture of Vitamins C and E on fertilization of tertiary butyl hydroperoxide-treated oocytes and parthenogenetic activation in the mouse. Theriogenology 2002;57:869-881. (Pubitemid 34303362)
15. Spector A, Ma W, Sun F, Li D, Kleiman NJ. The effect of H2O2 and tertiary butyl hydroperoxide upon a murine immortal lens epithelial cell line, alpha TN4-1. Exp Eye Res 2002;75:573-582. (Pubitemid 35435612)
16. Kennedy CH, Church DF, Winston GW, Pryor WA. Tert-Butyl-hydroperoxide induced radical production in rat liver mitochondria. Free Radic Biol Med 1992;12:381-387.
17. Guidarelli A, Clementi E, Sciorati C, Cattabeni F, Cantoni O. Calcium-dependent mitochondrial formation of a species mediating DNA single strand breakage in U937 cells exposed to sub-lethal concentrations of tert-butyl-hydroperoxide. J Pharmacol Exp Ther 1997;283:66-74. (Pubitemid 27438947)
18. Sarkar MK, Sil PC. Prevention of tertiary butyl hydroperoxide induced oxidative impairment and cell death by a novel antioxidant protein molecule isolated from the herb, Phyllanthus niruri. Toxicol In Vitro 2010 ; 24:1711-1719.
19. Sarkar MK, Kinter M, Mazumder B, Sil PC. Purification and characterisation of a novel antioxidant protein molecule from Phyllanthus niruri. Food Chem 2009;114:1405-1412.
20. Gacche RN, Gond DS, Dhole NA, Dawane BS. Coumarin Schiff-bases: as antioxidant and possibly anti-inflammatory agents. J Enz Inhib Med Chem 2006;21:157-161.
21. Blois MS. Antioxidant determination by use of a stable free radical. Nature 1958;29:1199-1200.
22. Nash T. The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. J Biochem 1953;55:416-421.
23. Siddhuraju P, Becker K. Antioxidant properties of various solvent extracts of total phenolic constituents from three different agroclimatic origins of drumstick tree (Moringa oleifera Lam.) leaves. J Agric Food Chem 2003;51:2144-2155.
24. Sarkar K, Sil PC. A 43kDa protein from the herb Cajanus indicus L. Protects thioacetamide induced cytotoxicity in hepatocytes. Toxicol In Vitro 2006;20:634-640.
25. Hansen MB, Nielsen SE, Berg K. Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill. J Immunol Methods 1989;119:203-210. (Pubitemid 19132276)
26. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248-254.
27. LeBel CP, Bondy SC. Sensitive and rapid quantitation of oxygen reactive species formation in rat synaptosomes. Neurochem Int 1990;17:435-440. (Pubitemid 20274589)
28. Kim JD, McCarter RJM, Yu BP. Influence of age, exercise and dietary restriction on oxidative stress in rats. Aging Clin Exp Res 1996;8:123-129.
29. Esterbauer H, Cheeseman KH. Determination of aldehydic lipid peroxidation products: malonaldehyde and 4-hydroxynonenal. Methods Enzymol 1990;186:407-421. (Pubitemid 20279982)
30. Uchida K, Stadtman ER. Covalent attachment of 4-hydroxynonenal to glyceraldehydes-3-phosphate dehydrogenase. J Biol Chem 1993;268:6388-6393.
31. Sinha M, Manna P, Sil PC. Taurine, a conditionally essential amino acid, ameliorates arsenic-induced cytotoxicity in murine hepatocytes. Toxicol In Vitro 2007;21:1419-1428. (Pubitemid 350103535)
32. Ji L, Liu T, Chen Y, Wang Z. Protective mechanisms of N-acetyl-cysteine against pyrrolizidine alkaloid clivorine-induced hepatotoxicity. J Cell Biochem 2009; 108:424-432.
33. Tapalaga D, Tiegs G, Angermüller S. NFkB and caspase-3 activity in apoptotic hepatocytes of galactosamine-sensitized mice treated with TNFα. J Histochem Cytochem 2002;50:1599-1609. (Pubitemid 36078125)
34. Mingatto FE, Rodrigues T, Pigoso AA, Uyemura SA, Curti C, Santos AC. The critical role of mitochondrial energetic impairment in the toxicity of nimesulide to hepatocytes. J Pharm Exp Therap 2003;303:601-607. (Pubitemid 35231231)
35. McCord JM. The evolution of free radicals and oxidative stress. Am J Med 2000;108:652-659. (Pubitemid 30336605)
36. Halliwell B. Antioxidants in human health and disease. Annu Rev Nutr 1996;16:33-50. (Pubitemid 26286845)
37. Chandra J, Samamli A, Orrenius S. Triggering and modulation of apoptosis by oxidative stress. Free Radic Biol Med 2000;29:323-333.
38. Fridovich I. Superoxide radical and superoxide dismutase. Acc Chem Res 1972;5:321-323.
39. Jones P, Suggett A. The catalase-hydrogen peroxide system. A theoretical appraisal of the mechanism of catalase action. Biochem J 1968;110:621-629.
40. Ketterer B. Detoxification reactions of glutathione and glutathione reductase. Xenobiotca 1986;16:957-975.
41. Rosenblat M, Aviram M. Macrophase glutathione content and glutathione peroxidase activity are inversely related to cell-mediated oxidation of LDL: in vitro and in vivo studies. Free Radic Biol Med 1998;24:305-317. (Pubitemid 28008809)
42. Baldwin AS. The NF-kappa B and I kappa B proteins: new discoveries and insights. Annu Rev Immunol 1996;14:649-683.
43. Akira S, Kishimoto T. NF-IL6 and NF-kB in cytokine gene regulation. Adv Immunol 1997;65:1-46.
44. Cowan KJ, Storey KB. Mitogen-activated protein kinases: new signalling pathways functioning in cellular responses to environmental stress. J Exp Biol 2003;206:1107-1115. (Pubitemid 36409152)
45. Yang SH, Sharrocks AD, Whitmarsh AJ. Transcriptional regulation by the MAP kinase signaling cascades. Gene 2003;320:3-21. (Pubitemid 37352751)
46. Song MO, Freedman JH. Activation of mitogen activated protein kinases by PCB126 (3,3′,4,4′, 5-Pentachlorobiphenyl) in HepG2 Cells. Toxicol Sci 2005;84:308-318.
47. Wu D, Cederbaum AI. Role of p38 MAPK in CYP2E1-dependent Arachidonic acid toxicity. J Biol Chem 2003;278:1115-1124. (Pubitemid 36790792)
48. Mohamed A, Abdelmegeed MA, Kim SK, Woodcroft KJ, Novak RF. Acetoacetate activation of extracellular signal-regulated kinase 1/2 and p38 mitogen-activated protein kinase in primary cultured rat hepatocytes: role of oxidative stress. JPET 2004;310:728-736. (Pubitemid 38988919)
49. Keeble JA, Gilmore AP. Apoptosis commitment-translating survival signals into decisions on mitochondria. Cell Res 2007;17:976-984. (Pubitemid 350261795)
50. Verzola D, Bertolotto MB, Villaggio B, Ottonello L, Dallegri F, Frumento G, Berruti V, Gandolfo MT, Garibotto G, Deferran G. Taurine prevents apoptosis induced by high glucose in human tuble renal cells. J Investig Med 2002;50:443-451. (Pubitemid 35278685)